α-Ionone

Formula: C₁₃H₂₀O
Molecular weight: 192.2973
IUPAC Standard InChI: InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+
IUPAC Standard InChIKey: UZFLPKAIBPNNCA-BQYQJAHWSA-N
CAS Registry Number: 127-41-3
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Species with the same structure:
- α-Ionone
- Ionone
Other names: 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)-; α-Cyclocitrylideneacetone; (E)-α-Ionone; trans-α-Ionone; 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, trans; 4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (E)-; (3E)-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one; α-(E)-Ionone; trans-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one; 3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (3E)-; Ionone; 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (α-ionone); 4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one; 4-(2,6,6-trimethylcyclohex-2-ene-1-yl)-but-3-ene-2-one
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Van Den Dool and Kratz RI, non-polar column, temperature ramp

Go To: Top, References, Notes

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5MS	DB-5	DB-5	DB-5	HP-5MS
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	He		He		He
Substrate
Column diameter (mm)	0.25	0.32	0.25	0.25	0.25
Phase thickness (μm)	0.25	0.5	0.25	0.25	0.25
T_start (C)	60.	40.	60.	60.	60.
T_end (C)	250.	265.	240.	220.	280.
Heat rate (K/min)	2.	7.	3.	3.	4.
Initial hold (min)	8.				5.
Final hold (min)	30.	5.
I	1427.	1456.	1426.	1426.	1433.
Reference	Benkaci-Ali, Baaliouamer, et al., 2007	Ruiz Perez-Cacho, Mahattanatawee, et al., 2007	Telascrea, de Araujo, et al., 2007	Bastos, Ishimoto, et al., 2006	Saroglou, Dorizas, et al., 2006
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	HP-5MS	HP-5	HP-5	ZB-5	HP-5MS
Column length (m)	30.	30.	30.	30.	30.
Carrier gas	H2	He	He	He	He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.32	0.25
Phase thickness (μm)	0.25	0.25	0.25	0.5	0.25
T_start (C)	50.	50.	50.	40.	60.
T_end (C)	285.	220.	250.	265.	250.
Heat rate (K/min)	4.3	3.	4.	7.	4.
Initial hold (min)			5.		2.
Final hold (min)		20.	15.	5.	20.
I	1421.	1430.	1437.	1426.	1426.
Reference	Vujisic L., Vuckovic I., et al., 2006	Xian Q., Chen H., et al., 2006	Mahattanatawee, Goodner, et al., 2005	Mahattanatawee, Rouseff, et al., 2005	Pino, Mesa, et al., 2005
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	DB-5MS	DB-5	HP-5MS	SPB-1	SE-30
Column length (m)	30.	25.	30.	37.	50.
Carrier gas	He	N2		He
Substrate
Column diameter (mm)	0.25	0.25	0.25	0.32	0.2
Phase thickness (μm)	0.25	0.25	0.25	0.25
T_start (C)	40.	75.	50.	100.	50.
T_end (C)	280.	210.	280.	250.	250.
Heat rate (K/min)	4.	3.	3.	8.	6.
Initial hold (min)	2.	10.	5.
Final hold (min)		1.
I	1427.	1426.	1426.	1413.	1417.
Reference	Mardarowicz, Wianowska, et al., 2004	bin Ahmad and bin Jantan, 2003	Demetzos, Angelopoulou, et al., 2002	Misharina, Samusenko, et al., 2002	Paramonov, Khalilova, et al., 2000
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary	Capillary	Capillary	Capillary	Capillary
Active phase	Methyl Silicone	DB-1	SPB-1	SPB-1	CP Sil 5 CB
Column length (m)	25.	60.	60.	60.	26.
Carrier gas	He	H2	He	He
Substrate
Column diameter (mm)	0.2	0.25	0.25	0.25	0.32
Phase thickness (μm)	0.3	0.25	0.25	0.25	1.25
T_start (C)	40.	50.	35.	35.	100.
T_end (C)	200.	250.	235.	235.	250.
Heat rate (K/min)	2.	2.5	2.	2.	10.
Initial hold (min)		5.	10.	10.
Final hold (min)			40.	40.
I	1410.	1405.	1401.	1401.	1428.
Reference	Píry, Príbela, et al., 1995	Stashenko, Villa, et al., 1995	Huang, Bruechert, et al., 1987	Huang, Bruechert, et al., 1987	Halket and Schulten, 1985
Comment	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI	MSDC-RI

Column type	Capillary
Active phase	CP Sil 5 CB
Column length (m)	26.
Carrier gas
Substrate
Column diameter (mm)	0.32
Phase thickness (μm)	1.25
T_start (C)	100.
T_end (C)	250.
Heat rate (K/min)	10.
Initial hold (min)
Final hold (min)
I	1434.
Reference	Halket and Schulten, 1985
Comment	MSDC-RI

References

Go To: Top, Van Den Dool and Kratz RI, non-polar column, temperature ramp, Notes

Benkaci-Ali, Baaliouamer, et al., 2007
Benkaci-Ali, F.; Baaliouamer, A.; Meklati, B.Y.; Chemat, F., Chemical composition of seed essential oils from Algerian Nigella sativa extracted by microwave and hydrodistillation, Flavour Fragr. J., 2007, 22, 2, 148-153, https://doi.org/10.1002/ffj.1773 . [all data]

Ruiz Perez-Cacho, Mahattanatawee, et al., 2007
Ruiz Perez-Cacho, P.; Mahattanatawee, K.; Smoot, J.M.; Rouseff, R., Identification of Sulfur Volatiles in Canned Orange Juices Lacking Orange Flavor, J. Agric. Food Chem., 2007, 55, 14, 5761-5767, https://doi.org/10.1021/jf0703856 . [all data]

Telascrea, de Araujo, et al., 2007
Telascrea, M.; de Araujo, C.C.; Marques, M.O.M.; Facanali, R.; de Moraes, P.L.R.; Cavalheiro, A.J., Essential oil from leaves of Cryptocarya mandioccana Meisner (Lauraceae): Composition and intraspecific chemical variability, Biochem. Syst. Ecol., 2007, 35, 4, 222-232, https://doi.org/10.1016/j.bse.2006.09.015 . [all data]

Bastos, Ishimoto, et al., 2006
Bastos, D.H.M.; Ishimoto, E.; Marques, M.O.M.; Ferri, A.F.; Torres, E.A.F.S., Essential oil and antioxidant activity of green mate and mate tea (Ilex paraguariensis) infusions, J. Food Comp. Anal., 2006, 19, 6-7, 538-543, https://doi.org/10.1016/j.jfca.2005.03.002 . [all data]

Saroglou, Dorizas, et al., 2006
Saroglou, V.; Dorizas, N.; Kypriotakis, Z.; Skaltsa, H.D., Analysis of the essential oil composition of eight Anthemis species from Greece, J. Chromatogr. A, 2006, 1104, 1-2, 313-322, https://doi.org/10.1016/j.chroma.2005.11.087 . [all data]

Vujisic L., Vuckovic I., et al., 2006
Vujisic L.; Vuckovic I.; Tesevic V.; Dokovic D.; Ristic M.S.; Janackovic P.; Milosavljevic S., Comparative examination of the essential oils of Anthemis ruthenica and A-arvensis wild-growing in Serbia, Flavour Fragr. J., 2006, 21, 3, 458-461, https://doi.org/10.1002/ffj.1681 . [all data]

Xian Q., Chen H., et al., 2006
Xian Q.; Chen H.; Zou H.; Yin D., Chemical composition of essential oils of two submerged macrophytes, Ceratophyllum demersum L. and Vallisneria spiralis L., Flavour Fragr. J., 2006, 21, 3, 524-526, https://doi.org/10.1002/ffj.1588 . [all data]

Mahattanatawee, Goodner, et al., 2005
Mahattanatawee, K.; Goodner, K.L.; Baldwin, E.A., Volatile constituents and character impact compounds of selected Florida's tropical fruit, Proc. Fla. State Hort. Soc., 2005, 118, 414-418. [all data]

Mahattanatawee, Rouseff, et al., 2005
Mahattanatawee, K.; Rouseff, R.; Filomena Valim, M.; Naim, M., Identification and aroma impact of norisoprenoids in orange juice, J. Agric. Food Chem., 2005, 53, 2, 393-397, https://doi.org/10.1021/jf049012k . [all data]

Pino, Mesa, et al., 2005
Pino, J.A.; Mesa, J.; Muñoz, Y.; Martí, M.P.; Marbot, R., Volatile components from mango (Mangifera indica L.) cultivars, J. Agric. Food Chem., 2005, 53, 6, 2213-2223, https://doi.org/10.1021/jf0402633 . [all data]

Mardarowicz, Wianowska, et al., 2004
Mardarowicz, M.; Wianowska, D.; Dawidowicz, A.L.; Sawicki, R., The influence of sample treatment on SPME extracts from conifers. I. Comparison of terpene composition in Engelmann Spruce (Picea engelmanii) using hydrodistillation, SPME and PLE, Annales Universitatis Mariae Curie-Sklodowska Lublin - Polonia, 2004, 59, 3, 25-42. [all data]

bin Ahmad and bin Jantan, 2003
bin Ahmad, F.; bin Jantan, I., Chemical constituents of the essential oils of Goniothalamus uvariodes King, Flavour Fragr. J., 2003, 18, 2, 128-130, https://doi.org/10.1002/ffj.1142 . [all data]

Demetzos, Angelopoulou, et al., 2002
Demetzos, C.; Angelopoulou, D.; Perdetzoglou, D., A comparative study of the essential oils of Cistus salviifolius in several populations of Crete (Greece), Biochem. Syst. Ecol., 2002, 30, 7, 651-665, https://doi.org/10.1016/S0305-1978(01)00145-4 . [all data]

Misharina, Samusenko, et al., 2002
Misharina, T.A.; Samusenko, A.L.; Belyaeva, N.V., Gas chromatographic and IR spectroscopic characteristics of tri- and tetramethylcyclohexenyl butenyl ketones, Russ. Chem. Bull. (Engl. Transl.), 2002, 51, 9, 1684-1688, https://doi.org/10.1023/A:1021347404479 . [all data]

Paramonov, Khalilova, et al., 2000
Paramonov, E.A.; Khalilova, A.Z.; Odinokov, V.N.; Khalilov, L.M., Identification and biological activity of volatile organic compounds isolated from plants and insects. III. Chromatography-mass spectrometry of volatile compoundsof Aegopodium podagraria, Chem. Nat. Compd. (Engl. Transl.), 2000, 36, 6, 584-586, https://doi.org/10.1023/A:1017563708858 . [all data]

Píry, Príbela, et al., 1995
Píry, J.; Príbela, A.; Durcanská, J.; Farkas, P., Fractionation of volatiles from blackcurrant (Ribes nigrum L.) by different extractive methods, Food Chem., 1995, 54, 1, 73-77, https://doi.org/10.1016/0308-8146(95)92665-7 . [all data]

Stashenko, Villa, et al., 1995
Stashenko, E.E.; Villa, H.S.; Combariza, M.Y., Comparative study of Colombian rue oils by high resolution gas chromatography using different detection systems, J. Microcolumn Sep., 1995, 7, 2, 117-122, https://doi.org/10.1002/mcs.1220070204 . [all data]

Huang, Bruechert, et al., 1987
Huang, T.-C.; Bruechert, L.J.; Hartman, T.G.; Rosen, R.T.; Ho, C.-T., Effect of lipids and carbohydrates on thermal generation of volatiles from commercial zein, J. Agric. Food Chem., 1987, 35, 6, 985-990, https://doi.org/10.1021/jf00078a030 . [all data]

Halket and Schulten, 1985
Halket, J.M.; Schulten, H.-R., Thick-film capillary column gas chromatography-field ionization mass spectrometry: A complementary technique for the rapid analysis of volatiles, J. Chromatogr., 1985, 322, 200-205, https://doi.org/10.1016/S0021-9673(01)97672-1 . [all data]

Notes

Go To: Top, Van Den Dool and Kratz RI, non-polar column, temperature ramp, References

Symbols used in this document:

T_end Final temperature

T_start Initial temperature
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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